Dendrimer-based multivalent methotrexates as dual acting nanoconjugates for cancer cell targeting

Eur J Med Chem. 2012 Jan;47(1):560-72. doi: 10.1016/j.ejmech.2011.11.027. Epub 2011 Nov 23.

Abstract

Cancer-targeting drug delivery can be based on the rational design of a therapeutic platform. This approach is typically achieved by the functionalization of a nanoparticle with two distinct types of molecules, a targeting ligand specific for a cancer cell, and a cytotoxic molecule to kill the cell. The present study aims to evaluate the validity of an alternative simplified approach in the design of cancer-targeting nanotherapeutics: conjugating a single type of molecule with dual activities to nanoparticles, instead of coupling a pair of orthogonal molecules. Herein we investigate whether this strategy can be validated by its application to methotrexate, a dual-acting small molecule that shows cytotoxicity because of its potent inhibitory activity against dihydrofolate reductase and that binds folic acid receptor, a tumor biomarker frequently upregulated on the cancer cell surface. This article describes a series of dendrimer conjugates derived from a generation 5 polyamidoamine (G5 PAMAM) presenting a multivalent array of methotrexate and also demonstrates their dual biological activities by surface plasmon resonance spectroscopy, a cell-free enzyme assay, and cell-based experiments with KB cancer cells.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Dendrimers / chemistry*
  • Folic Acid Antagonists / chemistry
  • Folic Acid Antagonists / pharmacology
  • Humans
  • KB Cells
  • Methotrexate / chemistry*
  • Methotrexate / pharmacology*
  • Molecular Conformation
  • Molecular Dynamics Simulation
  • Nanoconjugates / chemistry*
  • Surface Plasmon Resonance
  • Tetrahydrofolate Dehydrogenase / metabolism

Substances

  • Antineoplastic Agents
  • Dendrimers
  • Folic Acid Antagonists
  • Nanoconjugates
  • PAMAM Starburst
  • Tetrahydrofolate Dehydrogenase
  • Methotrexate